Charlestown Vacation Rentals

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Our top choices for Charlestown vacation rentals

Pet Friendly Ocean Front Private Beach Cottage

Pet Friendly Ocean Front Private Beach Cottage
Charlestown
9.6 out of 10, Exceptional, (29 reviews)
"We had a blast - great location, gorgeous beach!"
United States
Tara G.
The price is CA $672
CA $1,090 total
includes taxes & fees
Mar 10 - Mar 11
Pet Friendly Ocean Front Private Beach Cottage

Private Houseboat In Beautiful Newport Harbor

Private Houseboat In Beautiful Newport Harbor
Fifth Ward
9.4 out of 10, Exceptional, (16 reviews)
"What an awesome way to experience Newport - it was our first time on a houseboat and Daniel was so kind and informative during our stay. The best thing I can say is that I can not wait to visit again soon and stay on the Waterlily. "
United States
Khuram C.
The price is CA $615
CA $886 total
includes taxes & fees
Feb 8 - Feb 9
Private Houseboat In Beautiful Newport Harbor

Island House Newport

Island House Newport
4.0 star property
Bellevue Avenue Historic District
9.8 out of 10, Exceptional, (34 reviews)
"Clean new hotel good location easy parking "
United States
Chris
The price is CA $173
CA $269 total
includes taxes & fees
Feb 22 - Feb 23
Island House Newport

A Mystic Stay as Sweet as Apple Pie!

A Mystic Stay as Sweet as Apple Pie!
Old Mystic
10.0 out of 10, Exceptional, (7 reviews)
"Charming and unique destination! It felt like we were staying in a museum and enjoyed the comfort of the beds, linens and delicious apple pie. Definitely plan on returning! "
United States
Lacia S.
The price is CA $126
CA $276 total
includes taxes & fees
Feb 10 - Feb 11
A Mystic Stay as Sweet as Apple Pie!

New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

New England Hospitality at the Carriage House Mystic Vacation Rentals LLC
Old Mystic
10.0 out of 10, Exceptional, (19 reviews)
"The room was so comfortable and cozy! We had everything we needed and the location was perfect. "
United States
Elizabeth R.
The price is CA $114
CA $272 total
includes taxes & fees
Feb 10 - Feb 11
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

The Oar Cottage (24) · walk Mystic-Train/EV Lvl-2

The Oar Cottage (24) · walk Mystic-Train/EV Lvl-2
Stonington
10.0 out of 10, Exceptional, (5 reviews)
"Great stay with friends! "
United States
Danielle V.
The price is CA $135
CA $328 total
includes taxes & fees
Feb 10 - Feb 11
The Oar Cottage (24) · walk Mystic-Train/EV Lvl-2

Lakeside cottage overhanging the water, beautiful window views across the lake

Lakeside cottage overhanging the water, beautiful window views across the lake
Ledyard
9.8 out of 10, Exceptional, (221 reviews)
"This lakeside cottage did not disappoint! It was just as advertised: we enjoyed a fire pit on the top deck and the hot tub on the bottom deck. The views were beautiful! And it was perfectly located to Foxwoods, Mystic, Stonington, Groton, etc. We'll definitely be back! "
United States
Elizabeth O.
The price is CA $133
CA $329 total
includes taxes & fees
Feb 10 - Feb 11
Lakeside cottage overhanging the water, beautiful window views across the lake

Lakeside cottage ON the water with beautiful views up the lake!

Lakeside cottage ON the water with beautiful views up the lake!
Ledyard
9.8 out of 10, Exceptional, (193 reviews)
"It was just wonderful!"
United States
Anonymous traveller
The price is CA $163
CA $387 total
includes taxes & fees
Feb 12 - Feb 13
Lakeside cottage ON the water with beautiful views up the lake!

Adorable in-law studio w/private entrance-Minutes to downtown, 5 miles to beach!

Adorable in-law studio w/private entrance-Minutes to downtown, 5 miles to beach!
Westerly
9.4 out of 10, Exceptional, (11 reviews)
"It was sweet, small but roomy for 2.A C was wonderful in the hot day. All provisions served us well. "
United States
Mary Alice B.
The price is CA $164
CA $249 total
includes taxes & fees
Feb 10 - Feb 11
Adorable in-law studio w/private entrance-Minutes to downtown, 5 miles to beach!

Cottages with easy access to Newport, beaches, nature trails and vineyards

Cottages with easy access to Newport, beaches, nature trails and vineyards
Middletown
9.8 out of 10, Exceptional, (64 reviews)
"Nice clean comfortable spot for a couple nights stay!"
United States
Anonymous traveller
The price is CA $176
CA $232 total
includes taxes & fees
Feb 8 - Feb 9
Cottages with easy access to Newport, beaches, nature trails and vineyards

Beautiful Studio overlooking the Mystic River

Beautiful Studio overlooking the Mystic River
West Mystic
10.0 out of 10, Exceptional, (55 reviews)
"Great property and great hosts. "
United States
Peter A.
The price is CA $209
CA $268 total
includes taxes & fees
Feb 15 - Feb 16
Beautiful Studio overlooking the Mystic River

Dog Friendly Cottages w/ easy access to Newport, beaches, trails and vineyards

Dog Friendly Cottages w/ easy access to Newport, beaches, trails and vineyards
Middletown
9.8 out of 10, Exceptional, (174 reviews)
"Really enjoyed my stay"
Canada
Lucas
The price is CA $176
CA $232 total
includes taxes & fees
Feb 8 - Feb 9
Dog Friendly Cottages w/ easy access to Newport, beaches, trails and vineyards

Beach house walking distance to Second Beach

Beach house walking distance to Second Beach
Easton's Point
9.8 out of 10, Exceptional, (26 reviews)
"The house was clean, had every thing you could possibly need. Great location."
United States
Sarah S.
The price is CA $146
CA $724 total
includes taxes & fees
Feb 18 - Feb 19
Beach house walking distance to Second Beach

Charming 1845 Home in the Heart of Mystic – Walk to Everything!

Charming 1845 Home in the Heart of Mystic – Walk to Everything!
Mystic
9.8 out of 10, Exceptional, (161 reviews)
"Beautiful charming house , walking distance to Mystic shops and eateries. "
United States
Elizabeth M.
The price is CA $131
CA $342 total
includes taxes & fees
Feb 10 - Feb 11
Charming 1845 Home in the Heart of Mystic – Walk to Everything!

Plan Your Escape to the Cottage! Minutes to Mystic, Connecticut. This pet-friendly retreat has a private fenced-in rear garden patio. Your stay includes organic breakfast, firepit, hammock, and onsite hiking trails. Up to 2 well-behaved pets welcome!

Plan Your Escape to the Cottage! Minutes to Mystic, Connecticut. This pet-friendly retreat has a private fenced-in rear garden patio. Your stay includes organic breakfast, firepit, hammock, and onsite hiking trails. Up to 2 well-behaved pets welcome!
Ledyard
10.0 out of 10, Exceptional, (12 reviews)
"My husband and I stayed in the cottage with our fur baby and it was perfect. The cottage was very comfortable and very private."
United States
Kim S.
The price is CA $296
CA $369 total
includes taxes & fees
Feb 10 - Feb 11
Plan Your Escape to the Cottage! Minutes to Mystic, Connecticut. This pet-friendly retreat has a private fenced-in rear garden patio. Your stay includes organic breakfast, firepit, hammock, and onsite hiking trails. Up to 2 well-behaved pets welcome!

New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!

New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!
Westerly
9.8 out of 10, Exceptional, (12 reviews)
"Property was amazing...plenty of room for the whole family and close to the beaches and aquarium! We will be staying again! "
United States
Erin f.
The price is CA $185
CA $656 total
includes taxes & fees
Feb 22 - Feb 23
New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!

Unbeatable Downtown Mystic Location

Unbeatable Downtown Mystic Location
Groton
10.0 out of 10, Exceptional, (11 reviews)
"Location was amazing! We walked everywhere. "
United States
Meagan M.
The price is CA $173
CA $380 total
includes taxes & fees
Feb 10 - Feb 11
Unbeatable Downtown Mystic Location

Contemporary cottage minutes from the heart of town!

Contemporary cottage minutes from the heart of town!
South Kingstown
10.0 out of 10, Exceptional, (47 reviews)
"Beautiful location, loved the property space and privacy! "
United States
Dianna S.
The price is CA $246
CA $499 total
includes taxes & fees
Feb 9 - Feb 10
Contemporary cottage minutes from the heart of town!

Harbor View Landing, Mystic CT - The Cove Waterfront Cottage

Harbor View Landing, Mystic CT - The Cove Waterfront Cottage
West Mystic
9.8 out of 10, Exceptional, (17 reviews)
"We had a wonderful time, great place which was like a small resort. Beautiful views and it was quiet and so peaceful there. We’re looking forward to staying again."
United States
Michael V.
The price is CA $239
CA $307 total
includes taxes & fees
Feb 10 - Feb 11
Harbor View Landing, Mystic CT - The Cove Waterfront Cottage

South Kingston Serenity

South Kingston Serenity
Wakefield-Peacedale
8.0 out of 10, Very good, (15 reviews)
"Great place"
United States
Anthony B.
The price is CA $164
CA $460 total
includes taxes & fees
Feb 11 - Feb 12
South Kingston Serenity
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Charlestown Hotel Reviews

Find out more about Charlestown

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Charlestown. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Charlestown?

Yes, we offer vacation rentals in Charlestown close to Frosty Drew Observatory, or you can select a more remote option if you're looking for a relaxing stay. Charlestown is known for its beaches and golf courses. Make sure you have time to check out the parks and seafood restaurants during your trip.

What are some of the best vacation rentals that Charlestown has to offer?

SECLUDED WATERFRONT HOME WITH ROOM FOR ALL: This vacation home rental outside of Charlestown is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Charlestown?

Choose from 73 Expedia vacation rentals in Charlestown for a memorable vacation.

What can I see and do in Charlestown?

Family-friendly attractions include Frosty Drew Observatory and Fantastic Umbrella Factory, whereas Ninigret Park and Ninigret National Wildlife Refuge are a couple of great spots to enjoy the outdoors. Other places in town to visit include Charlestown Town Beach and East Beach.

What are vacation rentals like in Charlestown?

Vacation rentals are privately owned accommodations you can reserve for several days or longer in Charlestown. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a small group gathering.